1-oxo-1-methylbenzothiadiazin-3-amine | 113508-91-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻二嗪
• 英文名称: 1-oxo-1-methylbenzothiadiazin-3-amine
• 英文别名: 2-Methyl-2-oxo-2lambda6-thia-3,5-diazabicyclo[4.4.0]deca-1,3,5,7,9-pentaen-4-amine；2-methyl-2-oxo-2λ6-thia-3,5-diazabicyclo[4.4.0]deca-1,3,5,7,9-pentaen-4-amine
• CAS: 113508-91-1
• 化学式: C₈H₉N₃OS
• 分子量: 195.245
• InChiKey: GSYXETJRJUTDRK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  13
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  76.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  1-oxo-1-methylbenzothiadiazin-3-amine 在 sodium hydroxide 、 乙醇 作用下， 以 乙醇 为溶剂， 反应 40.0h， 生成 5-oxo-5-methylimidazo[3,4-b][1,2,4]benzothiadiazine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles

  摘要：

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.

  DOI：

  10.1021/jm00401a009
• 作为产物：
  描述：

  3-(tert-butylamino)-1-methyl-1λ⁴-benzo[e][1,2,4]thiadiazine-1-oxide 在 盐酸 作用下， 以 水 、 甲苯 为溶剂， 以86 %的产率得到1-oxo-1-methylbenzothiadiazin-3-amine
  参考文献：
  名称：

  钯催化级联反应合成 3-氨基取代的苯并噻二嗪氧化物

  摘要：

  通过应用钯催化的 2-叠氮基亚砜亚胺与异腈的级联反应，一步合成了多种 3-氨基取代的苯并噻二嗪氧化物。在使用非常低的催化剂负载的短反应时间后，观察到所需的杂环以良好到极好的收率。遵循此协议可以直接访问与药学相关的亚砜亚胺的前体。

  DOI：

  10.1039/d3gc00442b

文献信息

• AGER, IAN R.;BARNES, ALAN C.;DANSWAN, GEOFFREY W.;HAIRSINE, PETER W.;KAY,+, J. MED. CHEM., 31,(1988) N 6, 1098-1115
  作者：AGER, IAN R.、BARNES, ALAN C.、DANSWAN, GEOFFREY W.、HAIRSINE, PETER W.、KAY,+

  DOI：——

  日期：——
• US4100280A
  申请人：——

  公开号：US4100280A

  公开（公告）日：1978-07-11
• US4171361A
  申请人：——

  公开号：US4171361A

  公开（公告）日：1979-10-16
• Synthesis and oral antiallergic activity of carboxylic acids derived from imidazo[2,1-c][1,4]benzoxazines, imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles
  作者：Ian R. Ager、Alan C. Barnes、Geoffrey W. Danswan、Peter W. Hairsine、David P. Kay、Peter D. Kennewell、Saroop S. Matharu、Peter Miller、Peter Robson

  DOI：10.1021/jm00401a009

  日期：1988.6

  4H-Imidazo[2,1-c][1,4]benzoxazine-2-carboxylic acid (3) was found to possess potent activity in the IgE-induced rat passive cutaneous anaphylaxis model which may be predictive of clinical antiallergic activity. Compared to disodium cromoglycate (DSCG, 1), 3 was less active following iv administration but unlike DSCG showed very significant oral activity. To explore the structural requirements for this activity, a range of tricyclic compounds was prepared and their activities were measured. Individual 2-carboxylic acids derived from imidazo[1,2-a]quinolines, imidazo[1,2-a]quinoxalines, imidazo[1,2-a]quinoxalinones, pyrrolo[1,2-a]quinoxalinones, pyrrolo[2,3-a]quinoxalinones, and imidazo[2,1-b]benzothiazoles showed iv activities up to 10(3) times as potent as DSCG and many of them showed significant oral activity. From these, imidazo[1,2-a]quinoxaline-2-carboxylic acid 114 has been chosen for further development.
• Synthesis of 3-amino-substituted benzothiadiazine oxides by a palladium-catalysed cascade reaction
  作者：Renè Hommelsheim、Sandra Bausch、Robin van Nahl、Jas S. Ward、Kari Rissanen、Carsten Bolm

  DOI：10.1039/d3gc00442b

  日期：——

  A variety of 3-amino-substituted benzothiadiazine oxides were synthesised in a single-step by applying a palladium-catalysed cascade reaction of 2-azido sulfoximines with isonitriles. The desired heterocycles were observed in good to excellent yields after short reaction times using very low catalyst loadings. Following this protocol gives direct access to precursors for pharmaceutically relevant sulfoximines

  通过应用钯催化的 2-叠氮基亚砜亚胺与异腈的级联反应，一步合成了多种 3-氨基取代的苯并噻二嗪氧化物。在使用非常低的催化剂负载的短反应时间后，观察到所需的杂环以良好到极好的收率。遵循此协议可以直接访问与药学相关的亚砜亚胺的前体。